Alkylnicotinium arylsulfonate pesticide



Patented Dec. 21 1948 ALKYLNICOTINIUM ARYLSULFONATE PESTICIDE Charles F. I Saunders, Oreland,

Jr., Washington, Pa.,

tary of Agriculture Woodward, Abington, Donald H.

and Raymond C. Provost,

assignors to the United States of America as represented by the Secre- No Drawing. Application February 2, 1945,

Serial No. 575,880

9 (Jaime. (Cl. 167-34) (Granted under the act amended April 30, 1928; 3'10 0. G. 757) This application is made under the act of March 3, 1883, as amended by the act of-Aprll 30, 1928, and the invention herein described and claimed, it patented, may be manufactured and used by or for the Government of the United States of America for governmental purposes without the payment to us of any royalty thereon.

Our invention relates to new derivatives of nicotine, particularly alkylnicotinium arvlsulfonates, and a process for their preparation. These derivatives are valuable due to their surface active and non-volatile properties. They are desirable ingredients in those types of pesticidal compositions where such properties are needed and are in themselves effective pesticidai agents.

The alkylnicotinium arylsuliona'tes 01 this invention may be represented by the general formula B(RX)1I, in which 13 represents nicotine, R represents a monovalent alkyl group. X represents an aromatic monosulfonate, in particular the group ary1-SOa-, and 11. is an integer not greater than 2, R. and X of each RX grouping being linked to the same nitrogen atom oi! the nicotine nucleus. R may be a saturated alkyl group conta ning one or more carbon atoms, such as thyl, ethyl, butyl, octyl, lauryl, hexadecyl, and octadecyl; an unsaturated alkyl group, such as alyl and methallyl; a substituted unsaturated akyl group, such as beta-chlorallyl; a mono valent organic radical in which the carbon chain is interrupted by oxygen atoms, such as the radical obtained by removal of the hydrogen atom of the alcohol group oi butyl carbitol, diethyleneglycol, or trlethyleneglycol.

In the general formula given above, X represents the group obtained by the removal of the acidic hydrogen atom from a monosulfonated aromatic hydrocarbon and is exemplified by benzene sulionate, toluene sulfonate, naphthalene sulionate, and diphenyl sulionate. The aromatic nucleus may contain, in addition to the sulionate group, substituting groups, such as halogen, allsyl, alkoxy. nitro, and acyloxy radicals.

The alhylnicotlnium arylsulionates of this th vention are prepared by the reaction of nicotine with an alkyl ester of an aromatic monosullonic acid. For example, the reaction of (a) -dodecyl p-toluene sulfonate with nicotine in equimolecular proportions yields (nl-dodecyl nicotinium p-toluene sulionate.

The formation of alkylnicotinium arylsulionates oi the type B(RX)2 is exemplified by the formation of dimethyl nicotinium cli-ptoluene sulfonate from the reaction of nicotine 0! March 3, 1883, as

with methyl p-toluene sulfonate in the molecular ratio 01' l to 2, respectively.

The following examples will serve to illustrate further our invention:

Example 1 soluble in water, and melted at 148-l50 C. The I analytical content of sulfur corresponded with the theoretical amount for dimethyl nicotinium di(p-toluene sulfonate) Example 2 A mixture consisting of 25 g. n-dodecyl p-toluenesulfonate, 11.9 g. of nicotine, and 25 cc. 0! benzene was reacted and purified by extracting with petroleum. ether in the same manner as described in Example 1.

The viscous residue was freed of solvent under vacuum and the final product was a viscous water-soluble liquid. The analytical content of sulfur corresponded with that calculated tor (n) a dodecyl nicotinium p-toluenesulionate.

Example 3 A mixture consisting 01 35 g. of n-octadecyl ptoiuenesulionate, 13.37 g. oi nicotine audit cc. of benzene was heated under reflux in an oil bath maintained at 110 C. for 3.5 hours, 130 G. for 0.5 hour and 145 C. for 1.5 hours. The reaction product was purified and freed of solvent & in mample 2. The sulfur content of the compound corresponded to the calculated theoretical value for n-octadecyi nicotinium p-toluene sulionate.

Example 4 A mixture consisting of g. oi diethylene glycol monobutylether-p-toluene sulionate, 211% g. of nicotine, and cc. of benzene was reacted and purified in the same way as described in Example 3. The suliur content oi the recovered compound corresponded to the calculated theo retical value tor beta butoxy. beta (nicotiniurn p-toluene sullonatel -diethyl ether.

Example 5 them to the habitat of the insect or to a material which is liable to attack by the insect. They may be dissolved in a suitable solvent, such as water, acetone, kerosene, and so forth, and used as a spray, or mixed with some other form of carrier. such as clay, bentonite, diatomaceous earth, talc, and so forth.

Having thus described our invention, we claim:

1. An allq/lnicotinium arylsulfonate represented by the general formula B(RX), in which B represents nicotine, R represents a monovalent alkyl group, X represents the group arylS0a, and n is an integer not greater than 2, R and X of 'each RX grouping being linked to the same nitrogen atom of the nicotine nucleus.

2. The alkylnicotinium arylsulfonate of claim 1, wherein n is 1.

3. The alkylnicotinium arylsulfonate of claim 1, wherein n is 2.

4. The alkylnicotinium arylsulfonate of claim 1, wherein the group aryl-SOais p-toluene sulfonate.

I 5. (n) -Dodecyl nicotinium p-toluene suifonate.

6. Dimethyl nicotinium di(p-toluene sulfonate).

7. Methallyl nicotinium p-toluene sulfonate.

8. A process comprising reacting nicotine with an alkyl ester of an aromatic monosulfonic acid, whereby a nicotinium salt is produced in which the alkyl group and the aromatic monosulfonic radical are both attached to the same nitrogen atom of the nicotine nucleus.

.9. A pesticide comprising an alkylnicotinium arylsuli'onate and a carrier therefor, said alkylnicotinium arylsulfonate having the general formula max) 1:, in which 13 represents nicotine, R represents a monvalent alkyl group, X represents the group aryl-SOa--, and n is an integer not greater than 2, R and X of each RX grouping being linked to the same nitrogen atom of the nicotine nucleus.

The following references are of record in the file of this patent:

om'mn STATES PA'I'ENTS Number Name Date 2,212,519 'Gicsinger Aug; 27, 1940 2,232,662 Hockenyos Feb. 18, 1941' 

